Hydrochloric Acid → HCID 68523701, compound

HRID 884175Notes

Reaction equation

HRID 884175 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[C:5]([NH:7][C:8]1[CH:9]=[N:10][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21]Cl)=[CH:17][CH:16]=2)=[CH:12][CH:13]=1)=[O:6].C(N(CC)CC)C.[NH:34]1[CH2:39][CH2:38][S:37][CH2:36][CH2:35]1.Cl>CN(C=O)C.C(OCC)(=O)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[C:5]([NH:7][C:8]1[CH:9]=[N:10][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][N:34]3[CH2:39][CH2:38][S:37][CH2:36][CH2:35]3)=[CH:17][CH:16]=2)=[CH:12][CH:13]=1)=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 67164ThiomorpholineHCID 68525073HCID 68525073, compound

Product 1

HCID 68523701HCID 68523701, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
40 °C

Procedure

3,4-dichloro-N-[6-(4-chloromethylphenoxy)-pyridin-3-yl]benzamide (0.61 g, 1.5 mmol) was dissolved in DMF (5 mL). To the resulting solution were added triethylamine (0.84 mL, 6.0 mmol) and thiomorpholine (0.15 mL, 1.5 mmol), and this solution was stirred overnight at 40° C. The resulting reaction solution was concentrated under reduced pressure. To the residue was added ethyl acetate and washed with a saturated sodium bicarbonate solution and brine. The organic layer was dried over anhydrous magnesium sulfate and evaporated. This residue was purified by silica gel column chromatography (chloroform:methanol=80:1). The obtained solid (0.56 g, 1.18 mmol) was dissolved in ethyl acetate (50 mL), and a solution of 4 N hydrogen chloride in ethyl acetate (0.295 mL, 1.18 mmol) was added, and this solution was stirred for 1 hour at room temperature. The precipitated crystals were collected by suction filtration, and recrystallized from methanol, to thereby yield 0.38 g of the title compound.

Workup

  1. customThe resulting reaction solution
  2. concentrationwas concentrated under reduced pressure
  3. additionTo the residue was added ethyl acetate
  4. washwashed with a saturated sodium bicarbonate solution and brine
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThis residue was purified by silica gel column chromatography (chloroform:methanol=80:1)
  8. stirringthis solution was stirred for 1 hour at room temperature
  9. filtrationThe precipitated crystals were collected by suction filtration
  10. customrecrystallized from methanol

Sources & evidence

ORD record
ord-97165b02f7e14acba60724d5d157b387
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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